Catalytic Efficiency of Primary [beta]-Amino Alcohols and Their Derivatives in Organocatalysis

Chiral primary [beta]-amino alcohols, constuting adjacently positioned Brønsted base and Brønsted acid sites, are emerging as very valuable bifunctional organocatalysts in a wide array of asymmetric organic transformations. Primary [beta]-amino alcohols represent inexpensive alternatives to other primary amino organocatalysts such as chiral diamines and cinchona-alkaloid-derived primary amines, being easy to synthesize and air-stable and offering the potential for introduction of different functional groups and also for alteration of steric sites. Here we reveal the catalytic use of simple primary [beta]-amino alcohols and their derivatives as organocatalysts in Diels-Alder cycloaddition, aldol condensation, Michael addition, 1,3-dipolar cycloaddition, the Morita-Baylis-Hillman reaction, cascade cyclization, allylation of isatins, Friedel-Crafts alkylation and epoxidation of olefins.